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Boron trifluoride etherate → (2',3'-Dimethoxyphenyl)-1,3-dithiane

HRID 54119
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HRID 54119 반응식
[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[CH2:13]([SH:17])[CH2:14][CH2:15][SH:16].B(F)(F)F.CCOCC>C(Cl)Cl>[CH3:1][O:2][C:3]1[C:10]([O:11][CH3:12])=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]1[S:17][CH2:13][CH2:14][CH2:15][S:16]1
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참가 물질

5

반응물 3

HCID 8000Boron trifluoride etherateHCID 80131,3-PropanedithiolHCID 665812,3-Dimethoxybenzaldehyde

생성물 1

HCID 19961202(2',3'-Dimethoxyphenyl)-1,3-dithiane수율 98.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

A solution of 49.5 g (298 mmol) of 2,3-dimethoxybenzaldehyde and 48.4 g (447 mmol) of propane-1,3-dithiol in 800 mL of methylene chloride was cooled to 0° C. Boron trifluoride etherate (7.5 mL, 61 mmol) was added dropwise to the cooled solution and the reaction mixture was stirred at 0° C. for 0.5 h, then at ambient temperature for 18 h. The methylene chloride solution was washed with 2×200 mL of 10% aqueous sodium hydroxide solution, 200 mL of water and 100 mL of brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give 75 g (98% yield) of 2-(2',3'-dimethoxyphenyl)-1,3-dithiane, m.p. 119°-120° C.; 1H NMR (CDCl3) δ: 1.8-2.0 (m, 1H), 2.1-2.25 (m, 1H), 2.86 (t, 1H), 2.91 (t, 1H), 3.05-3.2 (m, 2H), 3.83 (s, 3H), 3.91 (s, 3H), 5.68 (s, 1H), 6.86 (dd, 1H), 7.07 (t, 1H), 7.19 (dd, 1H).

후처리

  1. waitat ambient temperature for 18 h
  2. washThe methylene chloride solution was washed with 2×200 mL of 10% aqueous sodium hydroxide solution, 200 mL of water and 100 mL of brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-9e37af040852451d94f75ca6292f41a0
출처 데이터셋
uspto-grants-1997_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05621133

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